GB768241A - New monoazo-dyestuffs and process for making them - Google Patents

New monoazo-dyestuffs and process for making them

Info

Publication number
GB768241A
GB768241A GB2043/54A GB204354A GB768241A GB 768241 A GB768241 A GB 768241A GB 2043/54 A GB2043/54 A GB 2043/54A GB 204354 A GB204354 A GB 204354A GB 768241 A GB768241 A GB 768241A
Authority
GB
United Kingdom
Prior art keywords
sulphonamide
benzene
aminobenzene
methyl
sulphonic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2043/54A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB768241A publication Critical patent/GB768241A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
    • C09B62/447—Azo dyes
    • C09B62/45—Monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
    • C09B62/66—Azo dyes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Coloring (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1 - Aryl - 3 - methyl - 5 - pyrazolones having a monoacylated sulphonamide group in the aryl nucleus are prepared by diazotizing an arylamine containing a monoacylated sulphonamide group, reducing the diazo compound to a hydrazine, for example with stannous chloride or sodium bisulphite, and condensing the hydrazine with an acetoacetic acid ester, the formation of the pyrazolone being completed without hydrolysis of the monoacylated sulphonamide group. Thus, 3-aminobenzene-1-N-(benzene sulphonyl)-sulphonamide is diazotized, reduced with sodium bisulphite to the hydrazine, and the hydrazine condensed with ethyl acetoacetate to give 1-phenyl-3-methyl-5-pyrazolone - 31 - N - (benzene sulphonyl) - sulphonamide; 4-amino- or 3-amino-4-chloro- or 4 - amino - 3 : 6 - dichloro - benzene - 1 - N - (benzene sulphonyl)-sulphonamides may be treated similarly to give the corresponding substituted pyrazolones. Many similar compounds are listed. 1 - Methyl - 4 - aminobenzene - 2 - sulphonic acid - b - (p - toluene sulphonyloxy) - ethylamide and 1 - methoxy - 2 - aminobenzene - 4 - sulphonic acid - b - (p - toluene sulphonyloxy) - ethylamide are prepared by reacting 1-methyl-4-acetylaminobenzene - 2 - sulphonic acid - b - hydroxyethylamide or 1 - methoxy - 2 - acetylaminobenzene - 4 - sulphonic acid - b - hydroxyethylamide with p-toluene sulphonylchloride, followed by hydrolysis to split off the acetyl group. The compounds described are used in the preparation of azo dyestuffs (see Group IV (c)).ALSO:The invention comprises monoazo dyestuffs, obtained from diazo components of the benzene series, which contain at least one monoacylated sulphonamide group and at least one group of the formula:-SO2 - (NH)n - 1-R - X (1) wherein R is an aliphatic residue, n is 1 or 2 and X is a labile sulphur-containing substituent (as hereinafter defined), the monoacylated sulphonamide group and the group of the stated formula being present, one in the residue of the diazo component and the other in the residue of the coupling component. Labile sulphur-containing substituents are defined as substituents which are easily split off in an alkaline medium such as a sulphuric or sulphonic acid ester group. The dyestuffs may be prepared by coupling the appropriately substituted diazo and coupling components in a not strongly alkaline medium. Acyl residues present in the monocylated sulphonamide groups include acetyl, n-butyl, benzoyl, p - tert. - butyl - or chloro-benzoyl and methane - or ethane - or n - butane - or benzene - or naphthalene - b - or p-methyl-benzene or o - or p - chlorobenzene - or 2:5 - dichlorobenzene - sulphonyl residues. Specified components containing monoacylated sulphonamide groups are; diazo components:- 1 - aminobenzene - 3 - or - 4 - N - acetyl - sulphonamide, 4 - methyl - or - methoxy - 1 - aminobenzene - 3 - N - benzoyl - sulphonamide, 1 - aminobenzene - 2 - N - (methanesulphonyl) - sulphonamide, 1 - aminobenzene - 2 - or - 3 - or - 4 - N - (p - toluene sulphonyl) - sulphonamide, 2 - chloro - 1 - aminobenzene - 5 - N - (benzenesulphonyl) - sulphonamide, 4 - methyl - 1 - aminobenzene - 2 - N -(benzene sulphonyl) - sulphonamide, 1 - amino2 - methylbenzene - 5 - N - (benzene sulphonyl), sulphonamide and 1 - amino - 2:6 - dichloro-benzene - 4 - N - (benzene sulphonyl) - sulphonamide; coupling components:- 1 naphthol - 4 - or - 5 - N - (acetyl or benzene sulphonyl) - sulphonamide, 2 - naphthol - 4 - or - 5 - or -6 - or - 7 - or - 8 - N - benzoyl - sulphonamide, 2 - aminonaphtalene - 6 - N - (benzene sulphonyl) - sulphonamide, 2 - amino - 8 - hydroxynaphthalene - 6 - N - (p - toluenesulphonyl or benzene sulphonyl or 2:5 - dichlorobenzoyl) - sulponamide, 1 - (a - naphthyl) - 3 - methyl - 5 - pyrazolone - 41 - N - acetyl-sulphonamide, 1 -phenyl - 3 - methyl - 5 - pyrazolone - 21 - or - 31- or - 41 - N - (p - toluene-sulphonyl or p - chlorobenzene - or benzene - or 211:511 - dichlorobenzene - sulphonyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 - chloro - 51 - N - (benzene sulphonyl) - sulphonamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21:61 - or - 21:51 - dichloro - 41 - N - (benzene - sulphonyl) - sulphonamide and 1 - acetoacetylaminobenzene - 2 - or - 3 - or 4 - N - (benzoyl or benzene sulphonyl) - sulphonamide. Specified components containing groups of formula (1) are; diazo components:-1 - aminobenzene-4 - sulphonic acid - b - (ethane sulphonyloxy) - ethylamide, 1 - aminobenzene - 3 - or - 4 - sulphonic acid - b - (benzene sulphonyloxy) - ethylamide, 1 - aminobenzene - 4 - sulphonic acid - g - (benzene sulphonyloxy or p - toluene sulphonyloxy) - proplyamide, 4 - methyl - 1 - aminobenzene - 3 - sulphonic acid - b - (p - toluene sulphonyloxy) - ethylamide, 2:5 - dichloro-1 - aminobenzene - 4 - sulphonic acid - b - (benzene sulphonyloxy) - ethylamide, 2 - methoxy - 1 - aminobenzene - 5 - b - (p - toluene sulphonyloxy) - ethylsulphone, 1 - aminobenzene - 2 - or 3 - or - 4 - b - (p - toluene sulphonyloxy) - ethyl sulphone and 4 - methyl - 1 - aminobenzene - 3 - sulphonic acid - b -(benzenesulphonyloxy) - ethylamide; coupling components:-2 - aminonaphthalene - 6 - sulphonic acid - b - (benzene sulphonyloxy) - ethylamide, 1 -naphthol - 4 - or - 5 - sulphonic acid - b - (benzene sulphonyloxy) - ethylamide, 2 - naphthol - 6 - sulphonic acid - b - (benzene sulphonyloxy) - ethylamide, 2 - naphthol - 6 - b - (benzene sulphonyloxy) - ethyl sulphone, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 21 - or - 31 - or - 41 - sulphonic acid - b - (benzene sulphonyloxy) - ethylamide, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulphonic acid - g - (benzene sulphonlyoxy) - propylamide, 1-phenyl - 3 - methyl - 5 - pyrazolone - 31 - or - 41 - b -(p - toluenesulphonyloxy) - ethylsulphone and 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulphonic acid - b - (p - toluenesulphonyloxy) - ethylamide. Dyestuffs containing a sulphonylated sulphonamide group may be made by reacting 1 mol of a dyestuff which contains a - SO2NH2 group and a hydroxyalkyl sulphone group or sulphonic acid N - hydroxylalkylamide group with at least 2 mols of a sulphonic acid halide such as tosyl chloride, benzene - or ethane - sulphonyl chloride so that the sulphonamide group and the hydroxy group are both acylated. The dyestuffs may be used to dye nitrogenous natural or artificial fibres such as leather, wool, silk, superpolyamides and superpolyurethanes. They dye wool in yellow shades. In examples dyestuffs are prepared using some of the components specified above, the following additional components being specified; diazo components, 1 - methoxy - 2 - aminobenzene - 4 - sulphonic acid - b - (p - toluenesulphonyloxy) - ethylamide and 1 - aminobenzene - 4 - b (benzene sulphonlyoxy) - ethyl sulphone; coupling components, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - N - (311:411-dichlorobenzene sulphonyl)- sulphonamide and 1 - phenyl - 3 - methyl - 5 - pyrazolone-41 - N - (ethanesulphonyl)- sulphonamide.
GB2043/54A 1953-01-28 1954-01-22 New monoazo-dyestuffs and process for making them Expired GB768241A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH332482T 1953-01-28

Publications (1)

Publication Number Publication Date
GB768241A true GB768241A (en) 1957-02-13

Family

ID=4502453

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2043/54A Expired GB768241A (en) 1953-01-28 1954-01-22 New monoazo-dyestuffs and process for making them

Country Status (5)

Country Link
US (1) US2773863A (en)
BE (1) BE526035A (en)
CH (1) CH332482A (en)
DE (1) DE1001437C2 (en)
GB (1) GB768241A (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB870948A (en) * 1958-10-29 1961-06-21 Ici Ltd New anthraquinone dyestuffs
CA699092A (en) * 1961-04-06 1964-12-01 Polaroid Corporation Photographic products, processes and compositions
US3218312A (en) * 1962-10-12 1965-11-16 Polaroid Corp Hydroquinonylsulfonyl azo dye developers
US4166059A (en) * 1971-04-02 1979-08-28 Crompton & Knowles Corporation Alkali-fast disazo disulfimide dyes
US4302387A (en) * 1979-12-05 1981-11-24 Eastman Kodak Company Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings
US4301068A (en) * 1979-12-05 1981-11-17 Eastman Kodak Company Azo dyes from a 2-aminothiophene having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydrocyalkyl) carbamoyl groups on its ring
US4301071A (en) * 1979-12-05 1981-11-17 Eastman Kodak Company Azo dyes from aniline having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring
US4302390A (en) * 1979-12-05 1981-11-24 Eastman Kodak Company Azo dyes with sulfate groups on the diazotized 2-amino thiazol and 5-amino isothiazol moiety and with aniline, tetrahydroquinoline and benzomorpholine couplers
US4301070A (en) * 1979-12-05 1981-11-17 Eastman Kodak Company Azo dyes from a 5-aminopyrazole bearing 1 to 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl) carbamoyl groups on its ring
US4374769A (en) * 1981-06-17 1983-02-22 Eastman Kodak Company Water-soluble tris phenyl bisazo dyes for polyamide fibers

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2261175A (en) * 1939-07-01 1941-11-04 Eastman Kodak Co Azo compounds and material colored therewith
US2390113A (en) * 1941-08-04 1945-12-04 Eastman Kodak Co Monoazo compounds
US2424493A (en) * 1943-09-02 1947-07-22 Chem Ind Basel Pyrazolone monoazo dyes containing polybasic acid esters of alkylene sulfones
US2518078A (en) * 1946-01-31 1950-08-08 Geigy Ag J R Monoazodyestuffs of the pyrazolone series free from sulfonic acid groups and a process of making same
US2606185A (en) * 1948-02-12 1952-08-05 Ciba Ltd Monoazo-dyestuffs of the pyrazolone series
DE821977C (en) * 1949-10-02 1951-11-22 Basf Ag Process for the production of azo dyes

Also Published As

Publication number Publication date
CH332482A (en) 1958-09-15
DE1001437B (en) 1957-01-24
BE526035A (en)
US2773863A (en) 1956-12-11
DE1001437C2 (en) 1957-07-04

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